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Cruel Intentions – 1999

Cruel Intentions is a film adaptation of Les Liasions dangereuses written in 1792 by Pierre Choderlos de Laclos. Sarah Michelle Gellar stars as the rich, manipulative, and selfish Kathryn who finds joy in other's pain. Revolving around wealthy high school students in New York, the movie has as much drama as a full season of Gossip Girl. Also starring the then real-life couple Ryan Phillippe and Reese Witherspoon, the movie opened at #2 in the box office won a Teen Choice Award for Best Film - Drama, and took home an MTV Movie Award for Best Kiss, shared between Sarah Michelle Gellar and Selma Blair.